UNCOMMON FORMATION OF SPIRO ORTHOESTERS IN THE BROMOMETHOXYLATION REACTION OF A 4-[(AROYLOXY)METHYL]-3-CEPHEM DERIVATIVE

被引：5

作者：

BALSAMO, A

BENVENUTI, M

LAPUCCI, A

MACCHIA, B

NENCETTI, S

ROSSELLO, A

MACCHIA, F

DOMIANO, P

DRADI, E

机构：

[1] UNIV PISA,IST CHIM FARMACEUT & TOSSICOL,VIA BONANNO 6,I-56100 PISA,ITALY

[2] UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,I-56100 PISA,ITALY

[3] UNIV PARMA,IST STRUTT CHIM,CNR,CTR STUDIO STRUTT DIFFRATTOMET,I-43100 PARMA,ITALY

[4] UNIV PARMA,IST CHIM ORGAN,I-43100 PARMA,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 06期

关键词：

D O I：

10.1021/jo00006a035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 4-[((p-nitrobenzoyl)oxy)methyl]-3-cephem derivative 4 with bromine in methanol afforded a mixture of the 3-bromo-4-methoxy adducts 5 and 6 and of the unexpected 4-spiro orthoesters 7 and 8. The structure and configuration of 7 and 8 were demonstrated through the determination of the solid-state structure of 7 and by H-1 and C-13 NMR studies and chemical transformations. The mechanism and the stereochemical outcome of the reaction are discussed.

引用

页码：2148 / 2153

页数：6

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[1] CAMBRIDGE CRYSTALLOGRAPHIC DATA CENTER - COMPUTER-BASED SEARCH, RETRIEVAL, ANALYSIS AND DISPLAY OF INFORMATION [J].